Ocean views, remarkable privacy, and direct access to one of Anastasia Island's most beautiful stretches of beach make life at 5189 Medoras Avenue a dream. Perched atop a high dune on an oversized 60' x 165' homesite, this property offers amazing views, seclusion, and coastal convenience. Surrounded by mature tropical landscaping, the home welcomes you with a massive 12' x 42' covered front deck where ocean breezes and Atlantic views become part of your daily routine. The elevated setting not only captures the views but also provides peace of mind with no flooding concerns. With ample room for a future pool and an exceptionally private backyard, there is plenty of space to create your own outdoor oasis. Concrete block construction, a metal roof, and Hardie Board siding provide lasting strength, while the craftsmanship throughout reflects an era when homes were built with longevity in mind. Two oversized 17' x 23' garages with 12-foot ceilings provide abundant space for vehicles, boats, golf carts, workshop space, and all the gear that comes with living near the water. Inside, high 11-foot ceilings and smooth finishes create an open, airy feel throughout the lower level. Two massive guest bedrooms and a full bath provide comfortable accommodations for family and friends, while direct access to the backyard enhances indoor-outdoor living. Upstairs, natural light fills the main living area where rich hardwood floors, a real wood-burning fireplace, and ocean views create an inviting atmosphere. The open-concept design connects the living room, dining area, and kitchen, making it easy to entertain while enjoying the coastal backdrop. Front and rear covered decks extend the living space outdoors, offering the perfect spots for morning coffee, afternoon relaxation, or evening sunsets. Beyond the home itself, the lifestyle is hard to match. Located in the RS-3 zoning district, the property allows nightly rentals, making it equally appealing as a primary residence, vacation home, or investment opportunity. With a beach access just steps away, a boat ramp only one mile away, and historic downtown St. Augustine just seven miles from your doorstep, you'll enjoy convenient access to everything that makes St. Augustine so desirable. Restaurants, shopping, grocery stores, and everyday conveniences are all just minutes away as well. Properties with this level of elevation, privacy, ocean views, rental flexibility, and proximity to both the beach and boating are becoming increasingly difficult to find. Experience the best of Anastasia Island living and schedule your private showing today. **Photos of backyard have been digitally enhanced**